


First Time's the Snake Charmer

by CentellaWrites



Category: Hazbin Hotel (Web Series)
Genre: Awkward First Times, Bisexual Sir Pentious (Hazbin Hotel), Biting, Double Penetration in One Hole, Enthusiastic Consent, Explicit Sexual Content, First Time, Fluff and Smut, He's a snake alright, I don't know haha, Making Out, Other, Sir Pentious has two dicks, Snakes, Tongues, Touchy-Feely, mild choking, smut and humor, vocal sex
Language: English
Status: Completed
Published: 2020-06-12
Updated: 2020-06-12
Packaged: 2021-03-03 22:01:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,200
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24682750
Author URL: https://archiveofourown.org/users/CentellaWrites/pseuds/CentellaWrites
Summary: Originally written March 2019.You and Sir Pentious have your first time. It's awkward and sexy all at once, as you just take the time to discover each other.
Relationships: Sir Pentious/Reader (Hazbin Hotel)
Kudos: 44





	First Time's the Snake Charmer

**Author's Note:**

> So my current obsession is Hazbin / Sir Pentious fics. And it aaaalllll started with this one.
> 
> Also if Pentious seems a bit to OOC in this one, the pilot hadn't been released yet and I was going off of more his flustery easily embarrassed personality Viv was teasing in livestreams lol.
> 
> Fun note I did have ["I Feel it Coming"](https://youtu.be/iIWoYaJRryw) in my head a lot when writing this.

He’d waited so long over his rotary, attempting with every fiber of his being to rotate the blades in the order of your number.

“It’s not that hard, it’s not that hard…” Pentious chanted to himself, rubbing his temples, his forked tongue slithering through his lips in a sigh. Slapping his own face, he raised a quivering claw towards the numbers and blacked out as the ringing and spinning and formation of those impending digits were rung, only coming to when the ringing on the other end stopped and you answered..

“Thought you’d never call.”

He gulped. Stunned silence. The phone fell out of his hands. “Confound it!” Catching it with his reflexive tail, he fumbled again and said, “That was not directed at you! I apologize, I - I’m! I’m still here!”

Seconds of nervous laughter and a bowtie adjustment later, silence. So you said, “Penny, it’s all good.”

“It most certainly is not, I’m making a fool of myself..”

“Naah,” you offered. “I’m actually glad you called...I’m doing the crossword. For some reason.”

With a grimace and a cocked brow, he remarked, “Nothing on the television again today? Or your...whatever it’s called, deathphone 10 or whichever number we’re on at the moment?” He made a point to accentuate the “h”s in all the “wh” words.

“You got me. Listening to music at the same time as the TV on, browsing Tumblr, and having about 3 different texting conversations going on gets old after a while. I like taking it back a couple centuries and living it simple every now and then.”

“Then I’m your man!” He stopped. “That came out wr - ”

“- right!” you cut him off. “It came out right, Penny!”

“I’m sorry.”

“No worries!”

“I’m not that old…”

“It’s okay! We’re all different ages here, I mean, it’s hell. What do you expect?” You giggled again.

“Only an IDIOT would invent something that didn’t have multiple tablet properties, so one  _ deserving _ of such a multiplicity of tasks, such as yourself, could partake. Whenever they wanted!”

“Bitter Steve Jobs got famous instead of you?”

“Steve who - ? OH, yes….he was the one with the phone right? Not that Norman Bates gentleman?”

“You’re thinking of Bill Gates!” you shouted, uproarious laughter coming out without restriction. He fell silent but giggled a little with you. “Hun, it’s okay. Plus, I mean, I could just listen to music but right now I’d much rather talk to you.” Your voice and giggles continued rippled through the snake and his scales rolled in a shiver. He was so struck with you.

“I - I - flattery again, eh?”

“I mean it!”

“You’re …. I’m - ”

An EggBoi poked his head through the door of Sir Pentious’ room and peeped, “Boss, we’re nearing the course to Ace Hardware, and if you wanna stop by your  _ lover’s _ place, it’s on the way!”

He was immediately silenced by the throwing of an anchor, hooked to a thick seemingly endless chain.

“What was that?” you asked from the other line.

“Kevin,” Pentious grumbled, pinching between his eyes. “What was it you needed? With the crossword?”

“Ah! Yeah, so … I’m stuck on one. Care to help with your vast vocabulary?”

“Please!”

“Awesome, so I need an 11-letter word for, like … excess? Useless excess?”

He pondered his personal word bank, muttering a few off the cuff. “Su - superfluous?”

“Thaaaat’s it,” you drawled.

“Yes, I knew that was the answer! Tis what the kids these days are now referring to as ‘extra’, no?”

“Yup, you’d be right, Penny.” You both shared a laugh, winding down with sighs. Awkward silence. “Soooo, what did you call about?”

“Um …” Heavens, he didn’t think he’d get this far. Oh god, oh god….how does he ask this? “I was just i-i-inquiring if you’d like to…” He sighed, forcing the words out through a shaking voice, a shaking hand, a shaking body. “Well, I know we haven’t quite been able to partake in casual meetings, especially um … physically …”

“Uh-huh,” you answered, slowly and with a smile, allowing him to finish.

“Would you happen to be free? Tonight? To come to my ship and … g-g-g-get to … g-get to know me … ” Another gulp. “More - ? Physically - ?”

Pause.

“I understand if not! Do not worry about me, it’s not a situation that requires pressure on you, especially if you do not feel the same, as I really … really do desire to...oh god … to get to know you? Physically? As well?”

Another pause. You were thinking.

He was sweating.

“Penny, I’d love to.”

The serpent had to cover the receiving end of his telephone to make sure you didn’t hear the inhuman squeel he let out.

* * * * *

He’s kissing you. He’s really kissing you.

You’re amazing. This grand infatuation, sparkling in his eyes as he stares into yours, along the tendons in your neck, down your spine, and when you spin around they travel to the collar of your shirt, itching to see it removed. Much like many other demons in hell, you’d taken the form much like your human form, but with minor additions to your facial features, body shape, and crown of your head. Your hair is shoulder length, rough ends, and instead of ears you’ve got downturned ears like those of a Scottish fold cat.

You feel along his padded shoulders with ease, slightly nervous but attentive movements to gauge where he feels. “How long since you’ve last, like, slept with someone?” you ask, now in the thick of it...the dinner you two shared was short lived, a bit rushed, since after seeing him so nervous, and after him seeing you so dolled up and presentable, you two couldn’t wait to start exploring each other.

“Um … forgive me, it’s embarrassing to say.” He maintains a quivering tone, holding back moans as you trace your fingers along his face, in the direction of his scales.

“I don’t care,” you giggle. “Once I went about 4 years?” You trace back to the memories. It’s been a couple years since you’d been dead, and at a now stagnant 28 years old, your sex life had always been on and off in your previous life. “Yeah, 4 years, without sex. It was a pain.” You place careful hands to his chest, feeling his accelerating breathes, hearing them through his parted lips. “God, I remember having so many lonely nights, just alone with only the memories of that last time I  _ fucked _ …” you whisper, leaning closer to him.

His vibrations are obvious, but he lets you lick the side of his face where his ears would be had he been human. He squints, tongue slithering between his lips, arms buckled up.

“You doing okay?” you ask.

“ _ Yes _ ,” he breathes, “Yes, but again, yes, forgive me, it’s been ….  _ much _ longer than 4 years, my - ” He coughs loudly. “- my dear.”

“How long? I’m just curious,” you laugh, nerves setting in but you  _ want _ this, he’s ready and you can tell. You’re itching. “I just would like to know so I can go slower or faster or whatever! I just want to make sure you’re comfortable…” you trail off, again tracing hands and fingers along his body from beneath his coat. You twiddle the bowtie playfully.

He breathes a small laugh, and then a high-pitched laugh with a gritted smile. “About since I died.” He pauses waiting for your ministrations. “To clarify...I haven’t necessarily been prioritizing the, um, act, since well. There’s no. Motivation to?”

“Have you tried?”

A drive is ignited suddenly. “You don’t understand,” with a laugh, he continued, “Hell is  _ destined _ for a different ruler, a change of pace if you will...perhaps some new BLOOD in the bloodline.” He continues, complete with a clenched fist. “Such preparation for my takeover requires FOCUS! The damned Lucifer family is a DISGRACE to this Nation of Satan and DESERVE to be dethroned as though it were a French barricade! No such distractions of the physical kind were...appropriate...in my um ...endeavors ...” He coughs, off from his tangent.

“Goddamn,” you moan.

A pause. “You - um …” He grimaces. “You’re not going to leave because of that, perchance?”

“Honestly, I just want to kiss you more.”

He stops. “Th-that worksss.” He hisses the last word, prepping his lips for the onslaught.

You curl your hand to the back of his head and push your lips together. Holding a chaste lip collision for a couple seconds, you slowly bring your hands up his hood, tickling the various eyes that part and close with the increasing relaxation. Then the kiss deepens; lips part on both sides, and he hesitantly lets his forked tongue penetrate between your teeth with a weird hissing you’ve only heard in movies before.

It’s an..unusual feeling. You were used to something muscular, something moist and thick and rough, something larger and more similar feeling to your own mouth. Instead, you’re met with a metallic, smooth, thin, delicate instrument, with a synesthetic end at the fork. You’re worried you’d swallow it, but it dances through your teeth like another creature itself, since you’re guessing it could not only sense you, feel you, and taste you, but smell you. It’s fast, it pokes in and out with that same hissing noise, it’s long enough to wrap entirely around your tongue and unwrap just as quickly. You feel entirely too rough with such a tactful appendage.

Pentious opens all his eyes and they roll back, breaking away from you for a breath. His tongue hangs out still, unable to retract. It traces the sharp end of his fangs, from which a drop of supposed venom pools. The edges of his hood are inching up and outward in increasing arousal.

“You…” you whisper, biting your lip. “I do kinda have some questions, though.”

“Please,” he says, bashfully brushing your hair off your shoulder.

“Don’t take these the wrong way.”

“Dear, I’ve had plenty a verbally abusive terf war, with MANY a snakecist comment..not much can pierce this armor.” He’s a bit timid as he says this, but walls are melting.

“So…” You cough. “Can you, like, smell with your tongue?”

He’s so used to this question that he answers, plainly, “In a sssense.” He smiles. “Do you get it?”

“Sense!” It took you a second to get his pun.

“No, seriously, I uh...it’s like smelling but more of a ssixth senssse. It’s a way of bringing me more in touch with my surroundings, as if they’re what they are but sensation is  _ magnified _ .”

“Are you  _ trying _ to get me super fucking horny?” you propose, breathless and smiling.

“Maybe?” he offers, lowering his head and smiling along with you.

“Another thing,” you ask after a quick kiss break. “Do you - ? Are you venomous?”

“W - ”

“Like, if you, HYPOTHETICALLY, bite my neck or something not that that would ever happen ever…” You laugh and while he is a bit blind to your sarcasm you see a snicker forming on the corner of his mouth as well. “Um … is it gonna do that thing I see on YouTube videos where the blood curdles and solidifies and … and …”

“Coagulates?” he provides.

“That,” you answer. “Do you do that?”

“Well, you are a demon, correct?” He rolls his “rr”.

You nod.

“Unless I am an angel, which I assure you I’m not..” He kisses your hand. “...you have nothing to worry about.”

“But it’ll hurt?”

“I don’t recall bites not hurting, inherently.” He drops your hand, retracting a bit of the suave move he’d taken a chance on earlier. “But I don’t have to!”

You’re paused, redder than you’d been thus far. And both of you had had at least 2 glasses of port each. After a shoulder rub, your whispering arousal vocalizes, “ _ I kind of like the danger _ …”

“Oh!” he says, eyes wide. “Oh…” His eyelids lower. He licks his fangs again.

You moan.

Lips meet again, this time a greater attempt at playing with his tongue is made. It feels so smooth, non-porous, like licking leather.

Likewise with him, your tongue, humanoid but thinner than a human tongue, is  _ fascinating _ . He submits to your wet muscle but explores, even opening his eyes to see your face in bliss. He’s trapped in the embrace of the senses, you’re overwhelming to him, the particles in your mouth and your breath and your voice hitting each nerve in his forked tongue, alerting him to your presence. For a good minute or 2, he can’t focus; you’ve taken over every sense in his brain.

You’re gripping the sides of his arms and finally clothes start to come off. His lower half is uncovered anyway, not much mystery there, but you can’t wait to show him your body. Your nipples pucker, large and the main attraction to your flat chest, and in the midst of removing your collared shirt his ivory-hard fingertips trace the curvature of your sides.

“I have an idea..” you susurrate.

He’s lowered his posture and now looks up to you, and a high-pitched squeak of a response is uttered.

You take his hand and place a finger into your mouth, but he pulls away for a moment. He’s grimacing like he doesn’t know how to vocalize when someone is unexpectedly physical. You’ve seen this behavior of his with his minions.

“It’s okay!” you encourage. He breathes and shakes off the timidity, then allows you to smooth your tongue over the claw, teasing the tip. You both maintain eye contact, you’re awaiting his non-verbal response. He closes his eyes, breathes in deeply, and allows you to continue.

You dip the digit into the back of your throat, keeping eyes locked on him. He blushes dark red, eyes wide, lips pursed. You snicker and continue, taking in another finger.

Removing the hand from your mouth, you smooth it over your body, over your neck, your chest, your nipple. He lets out a quivering breath and the eyelids lower again as his lips unpurse. His hood is at about halfway out, and it moves with his breathing rhythmically. When his tongue hangs out unconsciously, you point to it in a suggestive way, and look to him. He nods, consenting to the touch, and you attempt to wave the sensitive slitted muscle to your neck.

It dances like a piece of ribbon along your tendons, and you shiver, letting out louder and louder moans through the motions. “ _ Fff _ -” you suck the air through your teeth as he leans into these licks. “ _ Nnng..slower _ ..”

He obeys and continues down, trailing spit down the space between your chest, lacing your collarbone.

“ _ Oh, god _ ..” you beg.

His mind swarms with another bout of sensory overload, and he almost sees colours. He can smell and taste you in one lick, feeling the pulse of your boiling blood as though it were a rhythmic drug that similarly pounded through his own head.

After you’ve removed his coat, his bow-tie the only piece of clothing still on, you begin coaxing him to the floor, hardwood, well-kept. Except for the obvious trails of a sort of snake sebum he leaves behind when he slithers. You sit and continue feasting on each others’ mouths and bodies. You lick in both directions of his scales, towards and against, feeling the rough almost knife-like pattern when against and the tongue-like smoothness when towards. In his chest is another eye, which also emotes with him. It makes you feel continuously watched, a voyeuristic excitement ignited. You wonder if that too makes him more aware, and wonder how much his senses are flooding at the moment.

You look down to your partner for your answer. He’s barely able to keep his eyes off you, a glazed over wetness in the pink corneas and parted lips with one fang hanging out. He bites his bottom lip with another gulp, the fang digging into his deep silken black skin.

Your pants are off. He’s lowering his eyes to them. Your arousal prominent, dripping for him, a rich human shade not seen since he dropped into Hell.

“Wait…” he says, suddenly apprehensive again.

“Yeah?” you answer, rubbing his wrist. You idly continue keeping your hands all over him.

In heavy breaths, his hood rising and falling with them, he confesses, “I have another...unknown facet.”

“What’s that?”

He looks to the ceiling, fiddling with a soft flap of skin just below his lower abdomen, his cloaca. It’s bulging, and beneath its surface is a fleshy pink angled cock, pre leaking along the fat shaft from the proportionally thin head.

And next to it is..another. Identical, though thinner, straighter, pointing outward away from the other. Leaking more and more the more you stare at it.

“Oh!” you’re surprised, but… “Hell, I should have known this! What kind of internet history did I waste in those 28 years of life to not know that male snakes have 2 DICKS!”

He’s back to bashful with a roll of his eyes, his hood sunk like wet hair. “Aaaannnnd I should have known this would lead nowhere, goodbye!”

“Penny, I’m joking! I don’t care!” You tug along his hood.

“I knowww,” he drones, wising up to your sarcasm. “But...I still cannot help I sense you’re. Not. Quite? Ready?”

You laugh, eyelids lowering again. “Of course it’d hurt if we use them, like, RIGHT NOW… but jeeze.” You hook a finger to his bowtie, lowering him to your mouth again, his hood flaring. “Do you understand just  _ how hot I am just seeing those fat cocks in front of me? _ ”

“You...really?” He cups your jawline.

“ _ Oh fuck yes.. _ ”

“Yes,” he barks blankly, awkwardly. “ _ Fuck _ .” He tries blankly repeating you.

A seductive laugh rips through your body; you want him. And you want him  _ now _ .

Many rounds of mouthing, teasing, and touching later, you’re on top of him, and ready to sit atop his engorged pleasure. Sweat dripping down his face, his teeth grit and his hands clench towards the sides of his head. He breathes so rapidly you’d swear for a second he’s panicking rather than aroused. His eyes roll back with each hump of your arousal against the shaft of his left cock, tongue hanging between the fangs and his jaw slack and half-O-faced. You grasp the sides of his neck and bring him in for another sloppy kiss, releasing, biting his bottom lip, and then gripping his abdomen.

Your opening welcomes the slick cock, which has enough natural lubrication for an easy entry. Your ass reaches the hilt of the cock, already in with you barely feeling it. It’s fleshy and satisfying, unlike any other cock you’d fucked, and pulsates inside you with his heartbeat, having the time of its life.

“ _ Aaah _ ..” he babbles, squirming. His “h”s quiver and he whimpers as you slowly start riding him. The sounds you two make together are at first quiet breaths, slick fleshy wetness, and floorboard creaks. They then escalate to whines, from the both of you, his still high-pitched and breathy, yours harsh exhalations and periodic yells. His left cock fills you but sort of moves and fits through your opening like it’s alive, much like his tongue, exploring and feeling each pulsation of arousal through your core.

“ _ P-please..touch me, _ ” you beg, sliding a finger along his arm and bringing it to your face to nibble on his finger again.

He offers the end of his tail instead.

Continuing to prove multiple states of consciousness among his appendages, he allows his tail to traverse to your right ear. You lean into his touch, still slamming your body against his, widening more and more to his thick cock, allowing it to flood you deeper and deeper. The tail slowly wraps around your neck, sort of teasing a constriction, and the flood of adrenaline makes you grip onto the thick of his tail, nails digging.

“Mm?” he asks, barely coherent.

“ _ Mmm! _ ” you answer, nodding, and he tightens,  _ ever  _ so slightly.

It’s a colourful rush of emotions and visuals at your corneas as you ride yourself towards a short climax. You breathe melodically, dangerously, frantically, and his tail grip loosens.

Suddenly, the second neglected dick starts moving towards your opening, teasing while you continue moving.

“ _ H-hey! _ ” he shouts, dazed. His tail loops around your neck, off you, the imprint of his scales along your skin. It  _ snaps _ the head of his other cock, in discipline. “ _ Nnnot..yet! _ ” he grunts. He moves to finger it himself but stops when you start moving slower.

You raise your hips. His first cock slips from you, a lubricious mess, veins poking. “I’m ready..” you whisper.

His eyes widen again. He thinks he loves you.

The second cock takes its starting position next to the first. With gritted teeth, hair stuck to your damp forehead, and an anxiously aroused scream, you let both cocks inside you, squeezing, contracting, shaking from the intensity.

“Aaa _ AAAAAHHHhhhh _ \- FFF!” he answers, first in his falsetto, then growled. The tightness he feels is  _ amazing _ , tugging the skin, stimulating him to his fullest. He’d never, NEVER gotten this much satisfaction through other means..the tightness of another demon on his length like a whole other consciousness apart from the various others his snake body inhibits. It’s mesmerizing and he screams, over and over, to let you know this.

You’re cumming again, starting to return to his mouth and taste his tongue again. And you feel his engorged length start pumping and pulsating faster too, as he increases his speed upwards against your ass.

“ _ Pen! _ ” you repeat, trading breaths with him.

“ _ MMMMnnnmn...HEAVENS!”  _ he “curses”. “L-love, you’re - YOU’RE SO TIGHT!”

“ _ F-fuck _ , cum inside me, Penny, come on..you know you want to..”

“I do, I do..” Out comes the tongue again, the slack jaw, the eyes rolling back, hood previously flaring in full now draping in submission.

“Let it go, hun!  _ J-Jesus _ !” you spit.

“You can - you can take it?” he checks in.

“ _ Yess, dear Satan, yess! _ ”

He grips your arms, pushing all he can into you, till the base of his “hips” are right up against your opening. You’re well about to burst, and you’re ready to. Huffing, reaching for the end of his tail again, and kissing all along his neck, you start nearing the climax, ready to force it all.

Just in the last moments of yours and his arousal, his pupils disappear, he grabs you by the shoulders and suddenly, dislocating his jaw, bites down on your neck with a loud  _ HISSSSSSSSS _ . You  _ screech _ , moaning it out, a tear rolling down your cheek; you can feel the sharpest tip of the fangs pierce the outermost layer of your sweating flesh, but not digging so deep as to harm you. He convulses, makes the same sound he would if he was eating four course gourmet, and latches onto your skin, feeling the life beneath your veins.

You feel a harmless rush of an injection, a reality warping palpitation, swelling through both of your climaxes.

Neither of you make a single sound right as the climax hits, and you move both your bodies along with it. Then, he releases you with a pop, and 2 perforations leak blood down your chest, over the ridges of your nipples, and onto his own. The eye blinks the liquid off. You both sigh, loudly, enjoying each others noises and pants, and wanting to stay in the moment between having came and slowing down forever. Suspended together, sharing this otherworldly headspace and enjoyment of each others bodies. You feel the release of both his cocks, shooting cum through you almost like the previous venomous bite. This demon’s whole presence, when in the heat of the moment, embodied all the overt consciousness of sex, and he had released the full of it inside you.

You wipe your forehead, sweat pooling. Pentious exhales through the removal of his spent cocks from your opening, a pool of white cum spurting from the flesh and trailing down your leg. You lay on top of him, the rhythm of each others’ breaths harmonizing, pure skin on skin as the wave of dopamine and other chemicals flood through an invisible but very real connection.

The snake fidgets and reaches over to his coat, into the pocket, pulling out what looks like a laser pointer. He patches your bite wounds with it.

“No venom, huh?” you murmur.

“No, I can ...I can choose stun or poison..it’s rather obvious which one you got..huh..” His eyes roll back again, eyelids fluttering in a rush of afterglow.

“You were planning on that the whole time, weren’t you?”

“Well, perhaps only after you’d asked..” He snickers and brings you closer.

You snuggle into it. “That was... _ so hot _ .”

He smiles. He fist bumps the air. “Yes!” He laughs through harsh breaths. “I feel so too..I still got it!”

You giggle, nuzzling into his neck, rubbing his chest, trailing his jaw to form your mouth over his again.

After minutes and minutes and minutes go by, and the breathing calms, you spy something in the corner of the room.

“Penny?”

“Mm?”

“Is that a chain I see?”

His eyes widen. Lips pursed again. Dammit, the anchor!

You laugh, nuzzling closer to him. Maybe next time.

**Author's Note:**

> If you like this one, I have other [Sir Pentious / reader fics](https://archiveofourown.org/works/24684214) [right here!](https://archiveofourown.org/works/24684619)


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